Improved solubility, dissolution rate, and oral bioavailability of main biflavonoids from Selaginella doederleinii extract by amorphous solid dispersion

References

• Borba PAA, Pinotti M, de Campos CEM, et al. (2016). Sodium alginate as a potential carrier in solid dispersion formulations to enhance dissolution rate and apparent water solubility of BCS II drugs. Carbohydr Polym 137:350–9.
   PubMed Web of Science ®Google Scholar
• Brough C, Williams RO. (2013). Amorphous solid dispersions and nano-crystal technologies for poorly water-soluble drug delivery. Int J Pharm 453:157–66.
   PubMed Web of Science ®Google Scholar
• Chen B, Wang X, Lin D, et al. (2019). Proliposomes for oral delivery of total biflavonoids extract from Selaginella doederleinii: formulation development, optimization, and in vitro–in vivo characterization. Int J Nanomedicine 14:6691–706.
   PubMed Web of Science ®Google Scholar
• Chen B, Wang X, Zou Y, et al. (2018). Simultaneous quantification of five biflavonoids in rat plasma by LC-ESI-MS/MS and its application to a comparatively pharmacokinetic study of Selaginella doederleinii Hieron extract in rats. J Pharm Biomed Anal 149:80–8.
   PubMed Web of Science ®Google Scholar
• Choi YH, Chin YW, Yang SJ, et al. (2016). Isolation of a lignan-enriched fraction from Schisandra chinensis and its effective solubilization via poloxamer 407-based solid dispersion formulation. J Pharm Investig 46:133–8.
   Google Scholar
• Chinese Pharmacopoeia Commission. 2015. Pharmacopoeia of the People’s Republic of China. Shanghai, China: Chemical Technology Press.
   Google Scholar
• Coulerie P, Nour M, Maciuk A, et al. (2013). Structure-activity relationship study of biflavonoids on the Dengue virus polymerase DENV-NS5 RdRp. Planta Med 79:1313–8.
   PubMed Web of Science ®Google Scholar
• Gao D, Tang S, Tong Q. (2012). Oleanolic acid liposomes with polyethylene glycol modification: promising antitumor drug delivery. Int J Nanomed 7:3517–26.
   PubMed Web of Science ®Google Scholar
• He Y, Ho C. (2015). Amorphous solid dispersions: utilization and challenges in drug discovery and development. J Pharm Sci 104:3237–58.
   PubMed Web of Science ®Google Scholar
• Iwashita M, Hashizume K, Umehara M, et al. (2019). Development of nobiletin-methyl hesperidin amorphous solid dispersion: novel application of methyl hesperidin as an excipient for hot-melt extrusion. Int J Pharm 558:215–24.
   PubMed Web of Science ®Google Scholar
• Kanaujia P, Poovizhi P, Ng WK, Tan R. (2015). Amorphous formulations for dissolution and bioavailability enhancement of poorly soluble APIs. Powder Technol 285:2–15.
   Web of Science ®Google Scholar
• Kedi PBE, Meva FE, Kotsedi L, et al. (2018). Eco-friendly synthesis, characterization, in vitro and in vivo anti-inflammatory activity of silver nanoparticle-mediated Selaginella myosurus aqueous extract. Int J Nanomedicine 13:8537–48.
   PubMed Web of Science ®Google Scholar
• Li D, Qian Y, Tian YJ, et al. (2017). Optimization of ionic liquid-assisted extraction of biflavonoids from Selaginella doederleinii and evaluation of its antioxidant and antitumor activity. Molecules 22:586–602.
   PubMed Web of Science ®Google Scholar
• Li N, Taylor LS. (2018). Tailoring supersaturation from amorphous solid dispersions. J Control Release 279:114–25.
   PubMed Web of Science ®Google Scholar
• Li S, Yao H, Zhao M, et al. (2013). Determination of seven biflavones of Selaginella doederleinii by high performance liquid chromatography. Anal Lett 46:2835–45.
   Web of Science ®Google Scholar
• Li S, Zhao M, Li Y, et al. (2014). Preparative isolation of six anti-tumour biflavonoids from Selaginella doederleinii Hieron by high-speed counter-current chromatography. Phytochem Anal 25:127–33.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 46:3–26.
   PubMed Web of Science ®Google Scholar
• Liu H, Peng H, Ji Z, et al. (2011). Reactive oxygen species-mediated mitochondrial dysfunction is involved in apoptosis in human nasopharyngeal carcinoma CNE cells induced by Selaginella doederleinii extract. J Ethnopharmacol 138:184–91.
   PubMed Web of Science ®Google Scholar
• Mignet N, Seguin J, Ramos Romano M, et al. (2012). Development of a liposomal formulation of the natural flavonoid fisetin. Int J Pharm 423:69–76.
   PubMed Web of Science ®Google Scholar
• Mitragotri S, Burke PA, Langer R. (2014). Overcoming the challenges in administering biopharmaceuticals: formulation and delivery strategies. Nat Rev Drug Discov 13:655–72.
   PubMed Web of Science ®Google Scholar
• Mohammadi G, Hemati V, Nikbakht MR, et al. (2014). In vitro and in vivo evaluation of clarithromycin–urea solid dispersions prepared by solvent evaporation, electrospraying and freeze drying methods. Powder Technol 257:168–74.
   Web of Science ®Google Scholar
• Nam S, Lee SY, Kang WS, Cho HJ. (2018). Development of resveratrol-loaded herbal extract-based nanocomposites and their application to the therapy of ovarian cancer. Nanomaterials 8:384–97.
   Web of Science ®Google Scholar
• Organization for Economic Cooperation and Development (OECD). 2004. Test no. 117: guideline for the testing of chemicals, partition coefficient (N-octanol/water): HPLC method.
   Google Scholar
• Ogden PB, Dorsey JG. (2019). Reversed phase HPLC with high temperature ethanol/water mobile phases as a green alternative method for the estimation of octanol/water partition coefficients. J Chromatogr A 1601:243–54.
   PubMed Web of Science ®Google Scholar
• Onoue S, Uchida A, Takahashi H, et al. (2011). Development of high-energy amorphous solid dispersion of nanosized nobiletin, a citrus polymethoxylated flavone, with improved oral bioavailability. J Pharm Sci 100:3793–801.
   PubMed Web of Science ®Google Scholar
• Papay ZE, Kallai-Szabo N, Ludanyi K, et al. (2016). Development of oral site-specific pellets containing flavonoid extract with antioxidant activity. Eur J Pharm Sci 95:161–9.
   PubMed Web of Science ®Google Scholar
• Park HJ, Kim MM. (2019). Amentoflavone induces autophagy and modulates p53. Cell J 21:27–34.
   PubMed Web of Science ®Google Scholar
• Paudel A, Worku ZA, Meeus J, et al. (2013). Manufacturing of solid dispersions of poorly water soluble drugs by spray drying: formulation and process considerations. Int J Pharm 453:253–84.
   PubMed Web of Science ®Google Scholar
• Roos A, Chevallier C, Dormidontova EE, et al. (2003). Relation of glass transition temperature to the hydrogen bonding degree and energy in poly(N-vinyl pyrrolidone) blends with hydroxyl-containing plasticizers: 3. Analysis of two glass transition temperatures featured for PVP solutions in liquid poly(ethylene glycol). Polymer 44:1819–34.
   Web of Science ®Google Scholar
• Saroni Arwa P, Zeraik ML, Ximenes VF, et al. (2015). Redox-active biflavonoids from Garcinia brasiliensis as inhibitors of neutrophil oxidative burst and human erythrocyte membrane damage. J Ethnopharmacol 174:410–8.
   PubMed Web of Science ®Google Scholar
• Sui Y, Li S, Shi P, et al. (2016). Ethyl acetate extract from Selaginella doederleinii Hieron inhibits the growth of human lung cancer cells A549 via caspase-dependent apoptosis pathway. J Ethnopharmacol 190:261–71.
   PubMed Web of Science ®Google Scholar
• Sui Y, Yao H, Li S, et al. (2017). Delicaflavone induces autophagic cell death in lung cancer via Akt/mTOR/p70S6K signaling pathway. J Mol Med 95:311–22.
   PubMed Web of Science ®Google Scholar
• Tang J, Sun J, Cui F, et al. (2008). Self-emulsifying drug delivery systems for improving oral absorption of Ginkgo biloba extracts. Drug Deliv 15:477–84.
   PubMed Web of Science ®Google Scholar
• Vasconcelos T, Marques S, das Neves J, Sarmento B. (2016). Amorphous solid dispersions: rational selection of a manufacturing process. Adv Drug Deliv Rev 100:85–101.
   PubMed Web of Science ®Google Scholar
• Vippagunta SR, Wang Z, Hornung S, Krill SL. (2007). Factors affecting the formation of eutectic solid dispersions and their dissolution behavior. J Pharm Sci 96:294–304.
   PubMed Web of Science ®Google Scholar
• Vo CL, Park C, Lee BJ. (2013). Current trends and future perspectives of solid dispersions containing poorly water-soluble drugs. Eur J Pharm Biopharm 85:799–813.
   PubMed Web of Science ®Google Scholar
• Wang W, Kang Q, Liu N, et al. (2015). Enhanced dissolution rate and oral bioavailability of Ginkgo biloba extract by preparing solid dispersion via hot-melt extrusion. Fitoterapia 102:189–97.
   PubMed Web of Science ®Google Scholar
• Weerapol Y, Tubtimsri S, Jansakul C, Sriamornsak P. (2017). Improved dissolution of Kaempferia parviflora extract for oral administration by preparing solid dispersion via solvent evaporation. Asian J Pharm Sci 12:124–33.
   PubMed Web of Science ®Google Scholar
• Wilson V, Lou X, Osterling DJ, et al. (2018). Relationship between amorphous solid dispersion in vivo absorption and in vitro dissolution: phase behavior during dissolution, speciation, and membrane mass transport. J Control Release 292:172–82.
   PubMed Web of Science ®Google Scholar
• Yadav J, Korzekwa K, Nagar S. (2019). Impact of lipid partitioning on the design, analysis, and interpretation of microsomal time-dependent inactivation. Drug Metab Dispos 47:732–42.
   PubMed Web of Science ®Google Scholar
• Yang S, Shi P, Huang X, et al. (2016). Pharmacokinetics, tissue distribution and protein binding studies of chrysocauloflavone I in rats. Planta Med 82:217–23.
   PubMed Web of Science ®Google Scholar
• Yao H, Chen B, Zhang Y, et al. (2017). Analysis of the total biflavonoids extract from Selaginella doederleinii by HPLC-QTOF-MS and its in vitro and in vivo anticancer effects. Molecules 22:325–42.
   PubMed Web of Science ®Google Scholar
• Yao W, Lin Z, Wang G, et al. (2019). Delicaflavone induces apoptosis via mitochondrial pathway accompanying G2/M cycle arrest and inhibition of MAPK signaling cascades in cervical cancer HeLa cells. Phytomedicine 62:152973–85.
   PubMed Web of Science ®Google Scholar
• Yi T, Zhang J. (2019). Effects of hydrophilic carriers on structural transitions and in vitro properties of solid self-microemulsifying drug delivery systems. Pharmaceutics 11:267–80.
   PubMed Web of Science ®Google Scholar
• Yu DG, Li JJ, Williams GR, Zhao M. (2018). Electrospun amorphous solid dispersions of poorly water-soluble drugs: a review. J Control Release 292:91–110.
   PubMed Web of Science ®Google Scholar
• Yu H, Chang JS, Kim SY, et al. (2017). Enhancement of solubility and dissolution rate of baicalein, wogonin and oroxylin A extracted from Radix scutellariae. Int J Pharm 528:602–10.
   PubMed Web of Science ®Google Scholar
• Yu S, Yan H, Zhang L, et al. (2017). A review on the phytochemistry, pharmacology, and pharmacokinetics of amentoflavone, a naturally-occurring biflavonoid. Molecules 22:299–322.
   PubMed Web of Science ®Google Scholar
• Zhang Q, Polyakov NE, Chistyachenko YS, et al. (2018). Preparation of curcumin self-micelle solid dispersion with enhanced bioavailability and cytotoxic activity by mechanochemistry. Drug Deliv 25:198–209.
   PubMed Web of Science ®Google Scholar
• Zheng XK, Zhang L, Wang WW, et al. (2011). Anti-diabetic activity and potential mechanism of total flavonoids of Selaginella tamariscina (Beauv.) Spring in rats induced by high fat diet and low dose STZ. J Ethnopharmacol 137:662–8.
   PubMed Web of Science ®Google Scholar